Total Synthesis of (+)-Hitachimycin

Amos B. Smith; Thomas A. Rano; Noritaka Chida; Gary A. Sulikowski

doi:10.1021/jo00291a005

Total Synthesis of (+)-Hitachimycin

Amos B. Smith, Thomas A. Rano, Noritaka Chida, Gary A. Sulikowski

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

The first total synthesis of the macrocyclic antibiotic-antitumor agent (+)-hitachimycin (1) has been achieved via a convergent and efficient route (22 steps, 1.2% overall yield). The key transformation entailed a highly stereoselective, three-component coupling of (-)-5-methoxycyclopentenone (5) with a zincate derived from vinyl iodide 4a and aldehyde (-)-6.

Original language	English
Pages (from-to)	1136-1138
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	55
Issue number	4
DOIs	https://doi.org/10.1021/jo00291a005
Publication status	Published - 1990
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00291a005

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title = "Total Synthesis of (+)-Hitachimycin",

abstract = "The first total synthesis of the macrocyclic antibiotic-antitumor agent (+)-hitachimycin (1) has been achieved via a convergent and efficient route (22 steps, 1.2% overall yield). The key transformation entailed a highly stereoselective, three-component coupling of (-)-5-methoxycyclopentenone (5) with a zincate derived from vinyl iodide 4a and aldehyde (-)-6.",

author = "Smith, {Amos B.} and Rano, {Thomas A.} and Noritaka Chida and Sulikowski, {Gary A.}",

year = "1990",

doi = "10.1021/jo00291a005",

language = "English",

volume = "55",

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journal = "Journal of Organic Chemistry",

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AU - Smith, Amos B.

AU - Rano, Thomas A.

AU - Chida, Noritaka

AU - Sulikowski, Gary A.

PY - 1990

Y1 - 1990

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AB - The first total synthesis of the macrocyclic antibiotic-antitumor agent (+)-hitachimycin (1) has been achieved via a convergent and efficient route (22 steps, 1.2% overall yield). The key transformation entailed a highly stereoselective, three-component coupling of (-)-5-methoxycyclopentenone (5) with a zincate derived from vinyl iodide 4a and aldehyde (-)-6.

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Total Synthesis of (+)-Hitachimycin

Abstract

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